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Just to clarify a small detail in your timeline - you mentioned buying Bitcoin in 2021 and selling last month. Since we're in early 2025, that would actually be about 3-4 years of holding, making this definitely a long-term capital loss (which is good for tax purposes as Andre mentioned). For your specific situation with the ~$30 loss, you absolutely don't need to wait for the 1099-B to file your taxes. CashApp likely won't send one anyway since your sale amount was under $1,000. You can find your transaction history in the CashApp app under "Activity" - screenshot or download those records showing your purchase date, purchase amount, sale date, and sale amount. That's all you need for Form 8949 and Schedule D. Since this is a loss, it will actually help reduce your tax liability, so there's no reason to delay filing. The $30 loss might seem small, but every deduction counts toward your refund!
Thanks for that clarification on the timeline! I was getting confused about when exactly I bought vs sold. You're absolutely right - buying in 2021 and selling in early 2024 would definitely be long-term. I found my transaction history in CashApp like you suggested and can see all the details clearly. It's actually kind of reassuring to know that even though I lost money, at least it can help offset some other income on my taxes. I'm going to go ahead and file without waiting for any forms since it sounds like I have everything I need. Appreciate the detailed breakdown!
Just wanted to add my experience for anyone else in a similar situation. I had almost the exact same scenario last year - bought Bitcoin through CashApp in 2021 and sold at a small loss in 2024. Never received a 1099-B from them, but I went ahead and filed using my transaction records from the app. The key thing I learned is that you can actually download a CSV file of all your Bitcoin transactions directly from CashApp. Go to your profile, then "Privacy & Security," then "Download My Data." It takes a day or two to process, but you get a comprehensive file with all transaction details including dates, amounts, and fees. This makes filling out Form 8949 much easier than trying to screenshot individual transactions. Also, don't forget to include any fees CashApp charged in your cost basis - those small transaction fees can add up and increase your deductible loss. In my case, the fees actually made my loss about $15 higher than I initially calculated, which helped a bit more with the tax offset. The IRS accepted my return without any issues, and I got my refund on schedule. So definitely don't wait around for forms that probably aren't coming!
I've been through a similar situation with S-corp owned real estate, and I want to emphasize how critical it is to act quickly on the 1031 exchange option if you're considering it. The 45-day identification period starts the moment you close on your current property, not when you start thinking about doing an exchange. Here's what I learned the hard way: you need to have your qualified intermediary (QI) in place BEFORE you sign any purchase agreements. The QI needs to be a party to the original sale contract, or you'll need to assign your rights in the contract to them. You can't just decide to do a 1031 exchange after closing - the IRS is very strict about this. For finding a good QI, look for someone who is a member of the Federation of Exchange Accommodators (FEA) and has specific experience with entity-owned exchanges (not just individual exchanges). Ask them directly about their experience with S-corp exchanges and request references from similar transactions. One thing that hasn't been mentioned yet - if your S-corp has been taking depreciation on the properties, you'll face depreciation recapture at ordinary income tax rates (up to 25%) rather than capital gains rates, regardless of whether you do a 1031 exchange or not. The exchange defers the gain but doesn't eliminate the recapture entirely. Given your $175K projected gain and the complexity of S-corp taxation, I'd strongly recommend getting both a tax attorney AND a QI involved immediately. The consultation fees will be minimal compared to your potential tax savings, and time is working against you here. Don't make the same mistake I did of waiting too long to get professional help. The window for tax planning strategies closes quickly once you're committed to a sale timeline.
This is exactly the kind of detailed, actionable advice I needed to hear! Thank you for sharing your experience and the specific warnings about timing. I had no idea that the QI needs to be involved from the contract stage - that's a crucial detail that could have completely derailed any exchange opportunity if I'd waited much longer. We haven't signed anything yet, so there's still time to get this structured properly. The point about depreciation recapture is particularly sobering. Even with a 1031 exchange, we'd still face recapture taxes on all the depreciation we've claimed over the years. That's probably going to be substantial given that we've owned the properties since 2018. I'm definitely taking your advice about getting both a tax attorney and QI involved immediately. Do you have any recommendations for how to find a tax attorney who specializes in this area? I'm worried about ending up with another generalist who doesn't fully understand the S-corp complications. Also, when you mention FEA membership for qualified intermediaries - is there a directory or search function on their website to find members in my area? I want to make sure I'm vetting candidates properly and not just going with the first one I find online. The timeline pressure is real, but at least now I have a clear action plan instead of just spinning my wheels trying to figure this out alone.
One strategy that hasn't been discussed yet is considering a charitable remainder trust (CRT) if you have any philanthropic goals. This could be particularly effective given your large capital gain situation. With a CRT, your S-corp could donate the appreciated real estate to the trust, receive an immediate tax deduction, and then the trust sells the property without paying capital gains tax. You'd receive income payments from the trust for a specified period (or life), and the remainder goes to charity. This strategy works especially well when you're facing a large one-time gain like your projected $175K. The immediate charitable deduction could offset a significant portion of other income, and you'd convert the lump-sum gain into a stream of income over time. The downside is that you don't retain ownership of the property, and there are minimum payout requirements and administrative costs. But given the size of your gain and the limited time for other strategies, it might be worth exploring alongside the 1031 exchange options. You'd need to work with an attorney who specializes in charitable planning, but the potential tax savings could be substantial. Even if you're not particularly charitably inclined now, you might find it attractive compared to writing a massive check to the IRS. Just another tool to consider as you're evaluating all your options. The key is getting professional advice quickly since most of these strategies require advance planning and can't be implemented at the last minute.
One thing nobody's mentioned - if this is your first year doing Uber, make sure you're setting aside money for quarterly estimated taxes going forward. Got hit with a nasty penalty my first year because I didn't know this was a thing! Since Uber doesn't withhold taxes, you're supposed to pay as you go through the year.
Omg thank you for mentioning this! What exactly are the quarterly deadlines? And how much should I be setting aside? I had no idea this was required.
The quarterly deadlines are usually April 15, June 15, September 15, and January 15 of the following year. The general rule is you need to pay at least 90% of your current year's tax or 100% of last year's tax (whichever is smaller) to avoid penalties. For most drivers, setting aside 25-30% of your net income (after deducting expenses) is a good starting point. It depends on your tax bracket and whether you have other income though. The IRS has a form called 1040-ES that helps calculate what you owe, or you can use their online withholding estimator. I personally just use the IRS Direct Pay website to make my quarterly payments - it's pretty straightforward once you get the hang of it.
As someone who's been through this exact confusion, I want to emphasize how important it is to keep detailed records beyond just the 1099 forms. Uber's driver dashboard has a "Tax Information" section that breaks down your earnings month by month, which is super helpful for reconciling those confusing totals. One thing that really helped me was creating a simple spreadsheet tracking my weekly deposits vs what the forms showed. The 1099-K includes tips that passengers paid through the app, while the 1099-NEC covers things like quest bonuses and surge pricing incentives - that's why the numbers don't match your bank deposits exactly. Also, don't forget you can deduct more than just Uber's fees! Phone bills (portion used for work), car washes, parking fees when waiting for rides, and even snacks/water you provide to passengers can be business expenses. Keep receipts for everything. The key is being able to show these expenses were necessary for your rideshare business. The quarterly tax payments mentioned above are crucial - I learned this the hard way with a $800 penalty my first year. Good luck with your filing!
This is incredibly helpful! I never thought about deducting things like car washes and phone bills. Quick question - for the phone bill, do you just estimate what percentage you use for rideshare work, or is there a specific way the IRS wants you to calculate that? I'm on my phone constantly with the Uber app running so I'm thinking it might be a significant deduction.
I'm going through the exact same thing right now! Filed my Alabama return in early March and it's been almost 4 months of that dreaded "processing" status. Got my federal refund in less than 2 weeks, so I know there's nothing wrong with my banking info or anything like that. What's really frustrating is how Alabama seems to be the only state with this problem. I have friends in Tennessee, Georgia, and Florida who get their state stuff handled quickly (well, FL and TN don't even have state income tax, lucky them!). Meanwhile we're stuck waiting around like it's 1985 or something. I've pretty much given up checking the website daily since it never changes anyway. At this point I'm just hoping it shows up before Christmas! š But seriously, this thread has been super helpful - at least now I know I'm not alone and this is just Alabama being Alabama. Definitely going to look into adjusting my withholding for next year so I don't have to go through this waiting game again.
I'm so glad I found this thread! I'm also new to Alabama (moved here from Oregon last year) and I'm absolutely shocked at how slow this process is. Filed in mid-March and still waiting here at the end of June - that's over 3 months! In Oregon, I'd have my state refund within a month, sometimes even faster. The fact that the federal government can process millions more returns and still get refunds out in 2-3 weeks while Alabama takes forever with a fraction of the volume is just mind-boggling. I keep checking that useless website hoping for some update, but it's been "processing" since April with zero progress indicators. It's like they're intentionally trying to frustrate taxpayers! Definitely adjusting my withholding next year - I'd rather have my money throughout the year than deal with this stress every tax season.
This is my first year filing in Alabama after moving here from New Jersey, and WOW what a difference! In NJ I'd get my state refund within 4-6 weeks max, but I filed my Alabama return in March and I'm still waiting here in late June. The federal refund came through in 10 days like clockwork, so clearly the problem is 100% on Alabama's end. What's driving me crazy is that their website gives you absolutely no useful information - just that generic "processing" message that hasn't changed in months. At least give us some idea of progress or timeline! I called the tax office twice and couldn't even get through to a human. Reading through all these comments is both comforting and depressing. Comforting to know this is normal and not just my return that got lost somewhere, but depressing to realize this is just how things work here. Coming from a state that had their act together, this feels like going back in time 20 years. Definitely going to adjust my withholding next year so I don't have to deal with this waiting game again. Why give Alabama an interest-free loan when they clearly operate like they're still using abacuses to calculate refunds? š¤¦āāļø
Welcome to Alabama! š I moved here from California about 3 years ago and had the exact same shock. California would get my state refund out in 2-3 weeks, but here it's like they process returns with carrier pigeons. I'm currently on month 4 of waiting for this year's refund and have just accepted this is Alabama's version of "normal." The lack of any real status updates is definitely the most frustrating part - that "processing" message might as well say "we'll get to it when we feel like it." Your NJ experience sounds amazing compared to what we deal with here. Adjusting withholding is absolutely the way to go - I did that last year and it's been such a relief not having to play this waiting game anymore!
Chloe Zhang
Does anyone know if there's an income limit for claiming the child tax credit? I have 3 kids and heard that if you make too much you start losing the credit amount.
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Amaya Watson
ā¢Yes, there are income phaseout thresholds for the child tax credit. For 2025, the credit begins to phase out when your modified adjusted gross income (MAGI) exceeds $200,000 for single filers or $400,000 for married filing jointly. The credit is reduced by $50 for each $1,000 (or fraction thereof) by which your MAGI exceeds these thresholds. So unless you're earning above those amounts, you should be able to claim the full credit for all your children.
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Jake Sinclair
I had a similar situation with my two kids last year and was worried about the same thing. What helped me was understanding that the child tax credit is worth up to $2,000 per qualifying child, so with your 4 kids you could potentially get up to $8,000 in credits when you file. One thing to keep in mind though - if you reduce your withholding too much by claiming all 4 dependents on your W-4, you might end up with a smaller refund (or even owing money) even though you'll still get the child tax credit. The credit reduces your tax liability, but if you haven't had enough withheld throughout the year, it might not cover the full amount you owe. I'd suggest running the numbers with the IRS withholding calculator on their website to see what works best for your situation. You can play around with different scenarios - like claiming 2 dependents vs all 4 - to find the sweet spot where you get more money in your paychecks without creating a big tax bill in April.
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Rita Jacobs
ā¢This is really helpful advice! I'm in a similar boat with trying to balance getting more money now vs. not owing at tax time. Quick question - when you used the IRS withholding calculator, did you find it pretty accurate? I've heard mixed things about whether those online calculators actually work well for people with multiple kids. Also, do you remember roughly how much extra you ended up getting per paycheck when you adjusted your W-4? I'm trying to get a sense of whether it's worth the hassle of updating everything with HR.
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Drew Hathaway
ā¢I found the IRS withholding calculator to be pretty accurate, but it does require you to have a good understanding of your total expected income for the year and any other tax situations you might have. With multiple kids, it handled the calculations well - you just need to make sure you input all the right information about your dependents and their ages. As for the paycheck difference, I ended up getting about $180 more per paycheck when I went from claiming 0 dependents to claiming both my kids. That was with bi-weekly pay, so it added up to almost $4,700 more throughout the year in take-home pay. The trade-off was my refund was about $3,200 smaller, but I preferred having that extra money in my pocket each month rather than giving the government an interest-free loan. The hassle with HR was minimal - just had to fill out a new W-4 and submit it. Most payroll systems update pretty quickly, so you should see the change in your next paycheck or two after submitting it.
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